Photo by Robbie Martin

Search Great Diamond Island Cottage Rentals from CA $241

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Great Diamond Island Cottages

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Exterior

Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC

9.8 out of 10, Exceptional, (7)
"We recently rented this for a quick family vacation and it exceeded our expectations. Can't wait to go back next summer!"
Alluring 2-Bedroom Cottage in Delightful Old Orchard Beach with WiFi, AC
Little Miss Cottages
Exterior

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (87)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Exterior

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

10.0 out of 10, Exceptional, (3)
"We enjoyed our stay there .the cottage was clean loved the charm of the place. Host was very helpful. Will return again. "
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
WATERFRONT ON PETTENGILL POND
Exterior

WATERFRONT ON PETTENGILL POND

9.6 out of 10, Exceptional, (4)
"My kids and I loved our stay at the pond. We enjoyed kayaking and floating in the peaceful setting. "
WATERFRONT ON PETTENGILL POND
The Outlet House, Comfortable Cottage
Exterior

The Outlet House, Comfortable Cottage

9.8 out of 10, Exceptional, (43)
"We loved our stay here! The cottage was super clean and in a quiet area within walking distance to town and all the shops and restaurants. Check-in was simple and the hosts were very friendly and responded quickly. Would definitely stay again!"
The Outlet House, Comfortable Cottage
2 bedroom cottage
Smart TV

2 bedroom cottage

9.2 out of 10, Wonderful, (5)
"quiet, clean, short walk to beach"
2 bedroom cottage
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Property grounds

Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout

9.6 out of 10, Exceptional, (85)
"The setting was absolutely beautiful. Shawn was extremely responsive and went out of his away to be accommodating. Would highly recommend!"
Escape to Serenity: Your Private Maine Lakefront Awaits at Little Sebago Lookout
Cute cottage only a 10 min walk to the beach.
Exterior

Cute cottage only a 10 min walk to the beach.

10.0 out of 10, Exceptional, (10)
"Our stay was perfect. The house is really cute and well located for going to the beach."
Cute cottage only a 10 min walk to the beach.
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Property grounds

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

9.8 out of 10, Exceptional, (29)
"Nice little hidden gem of a place."
Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Exterior

Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path

9.2 out of 10, Wonderful, (74)
"Loved how close it was to the beach.. very sweet little cottage."
Coastal Cottage w/ Enclosed Front Porch, Pond View – By Beach & Bike Path
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Exterior

Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!

9.6 out of 10, Exceptional, (46)
"We enjoyed our visit"
Private, 1st Floor Cottage, 5 Minute Walk to Beach- Perfect for Families!
Large 2BD cottage 10 min to Pier & Beach Pets ok
Exterior

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.0 out of 10, Wonderful, (34)
"Easy walk into the board walk shopping area ! Private parking and owner was readily available for any issues or concerns....gas station and lobster pound close enough i walked to pick us up dinner....5 lobster fresh cooked $45 and we're still steaming hot by time i walked back to the house"
The price is CA $241
CA $424 total
includes taxes & fees
Sep 2 - Sep 3
Large 2BD cottage 10 min to Pier & Beach Pets ok
The Hidden Cove by Bayley Vacation Rentals
Exterior

The Hidden Cove by Bayley Vacation Rentals

9.8 out of 10, Exceptional, (23)
"Great stay"
The Hidden Cove by Bayley Vacation Rentals
Charming cottage short walk to beach!
Exterior

Charming cottage short walk to beach!

9.4 out of 10, Exceptional, (30)
"This cottage was just as advertised. It was nice and clean and we had a great stay there."
Charming cottage short walk to beach!
Nautical View by Bayley Vacation Rentals
Exterior

Nautical View by Bayley Vacation Rentals

10.0 out of 10, Exceptional, (18)
"Beautiful place!"
Nautical View by Bayley Vacation Rentals
Cheerful 1 bedroom cottage only 50ft from beach
Exterior

Cheerful 1 bedroom cottage only 50ft from beach

10.0 out of 10, Exceptional, (2)
"We loved the area. We loved the cottage feel. We only wished it had bigger fridge and a better cook top. Other then that it was great."
The price is CA $370
CA $542 total
includes taxes & fees
Sep 2 - Sep 3
Cheerful 1 bedroom cottage only 50ft from beach
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Terrace/patio

Charming 3BR, 1.5BA beachfront cottage with multi-level decks

9.2 out of 10, Wonderful, (36)
"Wonderful "
Charming 3BR, 1.5BA beachfront cottage with multi-level decks
Cozy Cottage with stunning views of Stover's Cove.
Exterior

Cozy Cottage with stunning views of Stover's Cove.

9.8 out of 10, Exceptional, (6)
"We loved our time at the Cozy Cottage. They have the space well stocked with laundry detergent, dish soap, and even toiletries! All the communication was smooth and fast replies. I would recommend staying here if you are visiting Harpswell! "
Cozy Cottage with stunning views of Stover's Cove.
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
Property grounds

Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront

10.0 out of 10, Exceptional, (1)
Charming 4-bedroom cottage with AC, WiFi on Little Sebago Lake waterfront
15B Great Location! Walk to Beach/Pier in 5 min-Cottage Sleeps 6;12 w/front unit
Outdoor dining

15B Great Location! Walk to Beach/Pier in 5 min-Cottage Sleeps 6;12 w/front unit

9.8 out of 10, Exceptional, (51)
"Great location only a few minutes away from the beach. Clean, comfortable, we enjoyed our stay!"
15B Great Location! Walk to Beach/Pier in 5 min-Cottage Sleeps 6;12 w/front unit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Great Diamond Island Hotel Reviews

Germaine Inn South Portland

Germaine Inn South Portland

10/10 Excellent
"Everything from Germaine Inn South Portland is pretty good rooms, facilities, pool etc.. I only whish they provide breakfast until 10AM instead of 9AM."
Ye Lin 2-night trip
Posted 20 hours ago
Germaine Inn South Portland